Ecofriendly autoxidation of castor oil/ricinoleic acid. Multifunctional macroperoxide initiators for multi block/graft copolymers

Ecofriendly autoxidation is a reaction of air oxygen with unsaturated organic molecules at room temperature. Castor oil and ricinoleic acid were ecofriendly autoxidized for 5 months to obtain castor oil macroperoxide with a Mn of 1935 g mol -1 (Pcast5m) and the ricinoleic acid macroperoxide initiator (Prici5m) with a Mn of 1169 g mol -1 . Peroxide groups thermally initiated the free radical polymerization of methyl methacrylate (MMA), n-butyl methacrylate (nBMA), and styrene (S). Peroxide formation in the oxidized castor oil and ricinoleic acid was confirmed using iodometric analysis, elemental analysis, and differential scanning calorimetry technique. Peroxide decomposition in both macroperoxide initiators was observed at 166 °C for Prici5m and 170 °C for Pcast5m. Hydroxyl groups of Pcast5m were reacted with methacryloyl chloride to obtain methacrylated castor oil macroperoxide (PcastMA). The polymerization rates of the obtained macroinitiators were compared. The polymerization rate order is Pcast5m > Prici5m > PcastMA. Polymerization of styrene by PcastMA resulted in an increase in molar masses and an increase in the polymerization time while those of the styrene polymerization by Pcast5m and Prici5m remained constant. Carboxylic acid groups were reacted with amine-terminated polyethylene glycol (PEG), polydimethyl siloxane (PDMS), and polytetrahydrofuran (PTHF) while the hydroxyl functionality initiated the ring-opening polymerization of ?-caprolactone (CL). Prici-PEG-PMMA, Prici-PS-PDMS, Prici-PS-PTHF, Pcast-PS-PCL, Pcast-PCL-PMMA, and Pcast-PS-PnBMA multiblock copolymers were prepared and characterized using spectrometric, thermal, and stress–strain measurement techniques. © 2019 AOCS

Eser Adı
[dc.title]
Ecofriendly autoxidation of castor oil/ricinoleic acid. Multifunctional macroperoxide initiators for multi block/graft copolymers
Yazar
[dc.contributor.author]
Hazer, Baki
Yazar
[dc.contributor.author]
Eren, Melike
Yayın Yılı
[dc.date.issued]
2019
Yayıncı
[dc.publisher]
Wiley-Blackwell
Yayın Türü
[dc.type]
article
Özet
[dc.description.abstract]
Ecofriendly autoxidation is a reaction of air oxygen with unsaturated organic molecules at room temperature. Castor oil and ricinoleic acid were ecofriendly autoxidized for 5 months to obtain castor oil macroperoxide with a Mn of 1935 g mol -1 (Pcast5m) and the ricinoleic acid macroperoxide initiator (Prici5m) with a Mn of 1169 g mol -1 . Peroxide groups thermally initiated the free radical polymerization of methyl methacrylate (MMA), n-butyl methacrylate (nBMA), and styrene (S). Peroxide formation in the oxidized castor oil and ricinoleic acid was confirmed using iodometric analysis, elemental analysis, and differential scanning calorimetry technique. Peroxide decomposition in both macroperoxide initiators was observed at 166 °C for Prici5m and 170 °C for Pcast5m. Hydroxyl groups of Pcast5m were reacted with methacryloyl chloride to obtain methacrylated castor oil macroperoxide (PcastMA). The polymerization rates of the obtained macroinitiators were compared. The polymerization rate order is Pcast5m > Prici5m > PcastMA. Polymerization of styrene by PcastMA resulted in an increase in molar masses and an increase in the polymerization time while those of the styrene polymerization by Pcast5m and Prici5m remained constant. Carboxylic acid groups were reacted with amine-terminated polyethylene glycol (PEG), polydimethyl siloxane (PDMS), and polytetrahydrofuran (PTHF) while the hydroxyl functionality initiated the ring-opening polymerization of ?-caprolactone (CL). Prici-PEG-PMMA, Prici-PS-PDMS, Prici-PS-PTHF, Pcast-PS-PCL, Pcast-PCL-PMMA, and Pcast-PS-PnBMA multiblock copolymers were prepared and characterized using spectrometric, thermal, and stress–strain measurement techniques. © 2019 AOCS
Kayıt Giriş Tarihi
[dc.date.accessioned]
2019-12-23
Açık Erişim Tarihi
[dc.date.available]
2019-12-23
Yayın Dili
[dc.language.iso]
eng
Konu Başlıkları
[dc.subject]
Castor oil
Konu Başlıkları
[dc.subject]
Ecofriendly autoxidation
Konu Başlıkları
[dc.subject]
Multiblock copolymer
Konu Başlıkları
[dc.subject]
Ricinoleic acid
Konu Başlıkları
[dc.subject]
Ring-opening polymerization
Künye
[dc.identifier.citation]
Hazer, B. ve Eren, M. (2019). Ecofriendly autoxidation of castor oil/ricinoleic acid. Multifunctional macroperoxide initiators for multi block/graft copolymers. Journal of the American Oil Chemists’ Society, 96(4), 421-432. doi:10.1002/aocs.12186
Haklar
[dc.rights]
info:eu-repo/semantics/closedAccess
ISSN
[dc.identifier.issn]
0003021X
Sponsor YAYINCI
[dc.description.sponsorship]
Bülent Ecevit Üniversitesi: -2017-72118496-01
Sponsor YAYINCI
[dc.description.sponsorship]
Acknowledgments This work was supported by the Bülent Ecevit University Research Funds (#BEU-2017-72118496-01 and #BEU – 2016 - 72118496 – 10). The Authors thank Serdar Çoban and Sıdıka Saraç Tabaklı (Cilas Kauçuk, Devrek, Zonguldak, Turkey) for stress– strain measurements. Finally, the Authors thank Yücel Mercimek for his technical support.
İlk Sayfa Sayısı
[dc.identifier.startpage]
421
Son Sayfa Sayısı
[dc.identifier.endpage]
432
Dergi Adı
[dc.relation.journal]
JAOCS, Journal of the American Oil Chemists' Society
Dergi Sayısı
[dc.identifier.issue]
4
Dergi Cilt Bilgisi
[dc.identifier.volume]
96
Tek Biçim Adres
[dc.identifier.uri]
https://dx.doi.org/10.1002/aocs.12186
Tek Biçim Adres
[dc.identifier.uri]
https://hdl.handle.net/20.500.12628/5248
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polymerization macroperoxide Pcast5m Prici5m ricinoleic castor Peroxide groups styrene initiated methacrylate analysis obtain PcastMA increase reacted glycol polyethylene amine-terminated remained Carboxylic constant Polymerization resulted masses Ecofriendly ?-caprolactone Pcast-PCL-PMMA techniques measurement stress–strain thermal spectrometric characterized prepared
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